cas 626-56-2, 3-Methylpiperidine | Articles data

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Method for preparing piperidine compound by reducing pyridine compound through hydrogen transfer
The invention discloses a method for preparing a piperazine compound through a hydrogen transfer reduction of a pyridine compound, belonging to the field of organic synthesis. Under mild conditions, pyridine derivatives are used as raw materials, oxazolidine is used as a hydrogen transfer reagent, and cheap transition metals such as copper, cobalt, silver, palladium and the like are used as catalysts for catalysis of a hydrogen transfer reaction on 1,2,3,4-substitution sites, so a series of hydrogen transfer reduction product piperidine compounds are prepared, wherein the oxazaborolidine is obtained by a reaction of amino acid with a tetrahydrofuran complex of borane. The method has the advantages that product yield is high, reaction conditions are mild, the general applicability of raw materials is good, a hydrogen transfer reagent is cheap and easy to obtain, and good reproducibility can still be shown after quantitative reaction is conudcted. Therefore, the method of the invention provides an effective scheme for the industrial production of other high-value compounds containing the structure in the future.
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Paragraph 0022; 0023; 0024; 0025; 0026

(2021/04/28)

Ceria supported Ru0-Ruδ+ clusters as efficient catalyst for arenes hydrogenation
Selective hydrogenation of aromatic amines, especially chemicals such as aniline and bis(4-aminocyclohexyl)methane for non-yellowing polyurethane, is of particular interests due to the extensive applications. To conquer the existing difficulties in selective hydrogenation, the Ru0-Ruδ+/CeO2 catalyst with solid frustrated Lewis pairs was developed for aromatic amines hydrogenation with excellent activity and selectivity under relative milder conditions. The morphology, electronic and chemical properties, especially the Ru0-Ruδ+ clusters and reducible ceria were characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electronic microscopy (SEM), X-ray photoelectron spectroscopy (XPS), CO2 temperature programmed desorption (CO2-TPD), H2 temperature programmed reduction (H2-TPR), H2 diffuse reflectance Fourier transform infrared spectroscopy (H2-DRIFT), Raman, etc. The 2% Ru/CeO2 catalyst exhibited good conversion of 95% and selectivity greater than 99% toward cyclohexylamine. The volcano curve describing the activity and Ru state was found. Owning to the “acidic site isolation” by surrounding alkaline sites, condensation between the neighboring amine molecules could be effectively suppressed. The catalyst also showed good stability and applicability for other aromatic amines and heteroarenes containing different functional groups.
Cao, Yanwei,Zheng, Huan,Zhu, Gangli,Wu, Haihong,He, Lin
supporting information
p. 770 - 774
(2020/08/24)

Powering Artificial Enzymatic Cascades with Electrical Energy
We have developed a scalable platform that employs electrolysis for an in vitro synthetic enzymatic cascade in a continuous flow reactor. Both H2 and O2 were produced by electrolysis and transferred through a gas-permeable membrane into the flow system. The membrane enabled the separation of the electrolyte from the biocatalysts in the flow system, where H2 and O2 served as electron mediators for the biocatalysts. We demonstrate the production of methylated N-heterocycles from diamines with up to 99 percent product formation as well as excellent regioselective labeling with stable isotopes. Our platform can be applied for a broad panel of oxidoreductases to exploit electrical energy for the synthesis of fine chemicals.
Al-Shameri, Ammar,Apfel, Ulf-Peter,Lauterbach, Lars,Nestl, Bettina M.,Petrich, Marie-Christine,junge Puring, Kai
supporting information
p. 10929 - 10933
(2020/05/04)

Cascade Biotransformation to Access 3-Methylpiperidine in Whole Cells
Synthesis of 3-methylpiperidine from 1,5-diamino-2-methylpentane in preparative scale is reported by using recombinant Escherichia coli cells expressing a variant of the diamine oxidase from Rhodococcus erythroprolis and an imine reductase from Streptosporangium roseum. Optimization of process parameters for cultivation and bioconversion led to substantial improvements in the initial laboratory procedure. The transformation of the methyl-substituted diamine substrate to the N-heterocyclic product was successfully scaled-up from shake-flask to a 20 L bioreactor with increased substrate concentrations. Remarkably, we obtained 67 % of 3-methylpiperidine product from 140 g substrate within 52 h.
Borlinghaus, Niels,Weinmann, Leonie,Krimpzer, Florian,Scheller, Philipp N.,Al-Shameri, Ammar,Lauterbach, Lars,Coquel, Anne-Sophie,Lattemann, Claus,Hauer, Bernhard,Nestl, Bettina M.
p. 5738 - 5742
(2019/07/16)

Hydrogenation of N-Heteroarenes Using Rhodium Precatalysts: Reductive Elimination Leads to Formation of Multimetallic Clusters
A rhodium-catalyzed method for the hydrogenation of N-heteroarenes is described. A diverse array of unsubstituted N-heteroarenes including pyridine, pyrrole, and pyrazine, traditionally challenging substrates for hydrogenation, were successfully hydrogenated using the organometallic precatalysts, [(η5-C5Me5)Rh(N-C)H] (N-C = 2-phenylpyridinyl (ppy) or benzo[h]quinolinyl (bq)). In addition, the hydrogenation of polyaromatic N-heteroarenes exhibited uncommon chemoselectivity. Studies into catalyst activation revealed that photochemical or thermal activation of [(η5-C5Me5)Rh(bq)H] induced C(sp2)-H reductive elimination and generated the bimetallic complex, [(η5-C5Me5)Rh(μ2,η2-bq)Rh(η5-C5Me5)H]. In the presence of H2, both of the [(η5-C5Me5)Rh(N-C)H] precursors and [(η5-C5Me5)Rh(μ2,η2-bq)Rh(η5-C5Me5)H] converted to a pentametallic rhodium hydride cluster, [(η5-C5Me5)4Rh5H7], the structure of which was established by NMR spectroscopy, X-ray diffraction, and neutron diffraction. Kinetic studies on pyridine hydrogenation were conducted with each of the isolated rhodium complexes to identify catalytically relevant species. The data are most consistent with hydrogenation catalysis prompted by an unobserved multimetallic cluster with formation of [(η5-C5Me5)4Rh5H7] serving as a deactivation pathway.
Kim, Sangmin,Loose, Florian,Bezdek, Máté J.,Wang, Xiaoping,Chirik, Paul J.
p. 17900 - 17908
(2019/11/19)

Cobalt-bridged secondary building units in a titanium metal-organic framework catalyze cascade reduction of N-heteroarenes
We report here a novel Ti3-BPDC metal-organic framework (MOF) constructed from biphenyl-4,4′-dicarboxylate (BPDC) linkers and Ti3(OH)2 secondary building units (SBUs) with permanent porosity and large 1D channels. Ti-OH groups from neighboring SBUs point toward each other with an O-O distance of 2 ?, and upon deprotonation, act as the first bidentate SBU-based ligands to support CoII-hydride species for effective cascade reduction of N-heteroarenes (such as pyridines and quinolines) via sequential dearomative hydroboration and hydrogenation, affording piperidine and 1,2,3,4-tetrahydroquinoline derivatives with excellent activity (turnover number ～ 1980) and chemoselectivity.
Feng, Xuanyu,Song, Yang,Chen, Justin S.,Li, Zhe,Chen, Emily Y.,Kaufmann, Michael,Wang, Cheng,Lin, Wenbin
p. 2193 - 2198
(2019/02/20)

An approach to the synthesis of 3-substituted piperidines bearing partially fluorinated alkyl groups
An approach to the synthesis of 3-substituted piperidines bearing partially fluorinated alkyl groups was proposed. The method was based on the DAST-mediated nucleophilic fluorination of easily available 2-bromopyridin-3-yl alcohols and ketones affording 2-bromo-3-(1-fluoroalkyl)pyridines and 2-bromo-3-(1,1-difluoroalkyl)pyridines, respectively, followed by catalytic hydrogenation. The hydrogenation step was studied with common heterogeneous Pd-, Pt-, and Rh-based catalyst. It was found that in the case of fluoroalkyl derivatives, the pyridine core reduction was accompanied by hydrodefluorination, which became a limitation of the strategy. Nevertheless, the method worked well with 1,1-difluoroalkyl derivatives
Subota, Andrii I.,Ryabukhin, Sergey V.,Gorlova, Alina O.,Grygorenko, Oleksandr O.,Volochnyuk, Dmitriy M.
p. 61 - 66
(2019/05/29)

PROMOTER FOR SELECTIVE NITRILE HYDROGENATION
Disclosed is a process for hydrogenating a dinitrile comprising contacting the dinitrile with hydrogen over catalyst comprising at least 90 wt.% iron in the presence of promoter comprising at least one selected from alkali metal and alkaline earth metal promoters.
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Paragraph 00100-00101

(2017/09/08)

AMMONIUM SALT, ELECTROLYTE FOR LITHIUM SECONDARY BATTERY, AND LITHIUM SECONDARY BATTERY USING THEM
PROBLEM TO BE SOLVED: To provide: ammonium salt with low viscosity; an electrolyte for a lithium secondary battery; and the lithium secondary battery. SOLUTION: This invention relates to an ammonium salt expressed by the following chemical formula (1). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT
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Paragraph 0079

(2017/12/01)

Catalytic hydrogenation of substituted pyridines with PtO2 catalyst
The challenging methodology for the hydrogenation of substituted pyridines with mild reducing catalyst PtO2 in glacial acetic acid as a protic solvent using clean hydrogen under 50 to 70 bar atmospheric pressure leads to the synthesis of piperidine derivatives is reported. All the hydrogenated compounds were characterized by 1H NMR and ESI-MS.
Sreenivasulu, Reddymasu,Ranganath, Kalluri Venkata Sri,Raju, Rudraraju Ramesh
p. 4358 - 4360
(2015/11/28)

PREPARATION OF METHYLPENTAMETHYLENEDIAMINE AND METHYLPIPERIDINE
Methyl-2-pentamethylenediamine and methyl-3-piperidine are prepared by hydrogenation of methylglutaronitrile in the presence of a catalyst including cobalt, chromium, and nickel, especially a catalyst based on Raney cobalt doped with nickel and chromium.
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Page/Page column 2

(2011/02/26)

PRODUCTION OF NITRILE COMPOUNDS
Organic compounds containing at least one site of ethylenic unsaturation are catalytically hydrocyanated and the medium of hydrocyanation is separated into desired linear organic compounds containing at least one nitrile function, e.g., 3-pentenenitrile, and undesired nitrile by-products, e.g., methylglutaronitrile, and the undesired nitrile by-products are hydrodenitrogenated into ammonia and at least one hydrocarbon compound under an absolute hydrogen pressure ranging from 0.1 to 10 MPa at a temperature ranging from 200° to 500° C. and in the presence of a hydrodenitrogenation catalyst.
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Page/Page column 3-4

(2011/04/24)

METHOD FOR PRODUCING N,N-SUBSTITUTED-1,3-PROPANDIAMINES
The present invention relates to a process for preparing N,N-substituted 1,3-propanediamine by a) reacting secondary amine with acrolein at a temperature of from (?50) to 100° C. and a pressure of from 0.01 to 300 bar, andb) reacting the reaction mixture obtained in stage a) with hydrogen and ammonia in the presence of a hydrogenation catalyst at a temperature of from 40 to 400° C. and a pressure of from 1 to 400 bar, wherein the molar ratio of secondary amine to acrolein in stage a) is 2:1 or more and the hydrogenation catalyst used in stage b) comprises cobalt. In a preferred embodiment, acrolein which has been obtained from glycerol based on renewable raw materials is used. The invention further relates to the use of N,N-dimethyl-1,3-propanediamine (DMAPA) based on renewable raw materials as a feedstock for lubricant soaps and other detergents, coagulants, polymers and comb polymers. In a further preferred embodiment, stage b) is performed in the presence of water.
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Page/Page column 9

(2011/04/18)

METHOD FOR THE PREPARATION OF 3-METHYLPYRIDINE
The present invention relates to a method for the preparation of 3-methylpyridin by reacting 2-methyl-2,5-diaminopentane and/or 3-methylpiperidin at about atmospheric pressure and a temperature of 180°C to 400°C in a hydrogen atmosphere free of oxygen gas in the presence of a suitable catalyst and of water and/or a volatile alcohol.
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Page/Page column 3-4

(2010/04/27)

Ru/C catalyzed cyclization of linear α,ω-diamines to cyclic amines in water
A facile and convenient way to prepare cyclic amines in water was achieved by the catalyst system composed of Ru/C and Al powder. The α,ω-diaminoalkanes, 1,4-diaminobutane, 1,5-diaminopentane, and 1,6-diamino-heptane were converted to corresponding cyclic amines in good yields. The use of D2O provided a novel route to obtain deuterated cyclic amines in good yields.
G?dda, Thomas M.,Yu, Xiao-Yan,Miyazawa, Akira
experimental part
p. 1249 - 1253
(2010/03/30)

IONIC LIQUIDS AS ELECTROLYTES
The invention relates to an ionic liquid composition and a method for preparing the ionic liquid. The ionic liquid comprises a cation containing the FormulaI, disclosed, and wherein: n is 1 or 2, R1 is selected from the group consisting of: H, C1 - C12 alkyl, aryl or together with R2 may form a heterocyclic ring, and R2 is selected from the group consisting of: H, C1 - C12 alkyl, aryl or together with R1 may form a heterocyclic ring, and R3 is selected from the group consisting of hydrogen and C1-C12 alkyl, wherein if n is 1, then R3 is C1-C12 alkyl; and wherein R1 and R2 are not simultaneously selected from hydrogen. The method for the preparation of the ionic liquid composition provided herein starts with at least one N-substitution of the compound of Formula II, as herein disclosed, and wherein: n is 1 or 2, R3 is selected from the group consisting of hydrogen and C1-C12 alkyl, wherein if n is 1, then R3 is C1-C12alkyl. Further provided is a use of the ionic liquid in a chemical method including at least a method for electro-chemical oxidation.
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Page/Page column 18

(2009/01/24)

Benzothiazole derivatives with activity as adenosine receptor ligands
The present invention relates to substituted benzothiazole derivitives and to their pharmaceutically acceptable salts useful for the treatment of diseases related to the adenosine receptor.
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(2008/06/13)

Titanocene(III) catalyzed homogeneous hydrosilation-hydrogenation of pyridines
The homogeneous catalytic hydrosilation-hydrogenation of pyridines is observed in the presence of Cp2TiMe2 (Cp = η5-C5H5) and CpCp*TiMe2 (Cp* = η5-C5Me5) as catalysts and using PhSiH3 or PhMeSiH2 as the source of Si-H. Under appropriate conditions, and with appropriate ring-substitution, good yields of the N-silyldihydropyridine or N-silyltetrahydropyridine products are be obtained. Although complete saturation is not achieved with organosilane alone, carrying out the reaction under moderate H2 pressures can give excellent yields of N-silylpiperidines. Under moderate pressures of H2, [Cp2TiH]2 catalyzes rapid H-D exchange between H2 and the 2- and 6-positions of C5D5N. Under the same conditions, only traces of hydrogenation are observed. This, together with the regioselectivity of 3-picoline hydrosilation-hydrogenation, leads to the conclusion that the key step in the reaction is probably addition of Ti-Si to C=N.
Harrod,Shu,Woo,Samuel
p. 1075 - 1085
(2007/10/03)

Selective intramolecular cyclization of terminal (α,ω)- diamines to saturated heterocyclics over modified zeolites
The intramolecular cyclization of (α,ω)- diamines to heterocyclics has been carried out over modified zeolites. In the reaction of 2-methyl 1,5- diaminopentane over various zeolites at 300°C, the yields of 3- methylpiperidine have been found to be >95% at >95% conversion. In the cyclization of 1,6-diaminohexane to hexamethyleneimine over zeolites at 400°C, the yields of hexamethyleneimine are 86-95% at >96% conversion. Similarly in the reaction of 1,4-diaminobutane over ZSM-5 at 300°C, the yields of pyrrolidine are ~94% at >97% conversion. The effects of various reaction parameters like reaction temperature, weight hourly space velocity, mole ratio, time on stream, various catalysts have been studied.
Radha Rani,Srinivas,Kulkarni,Raghavan
p. 286 - 290
(2007/10/03)

14-substituted marcfortines and derivatives useful as antiparasitic agents
There are disclosed 14α-hydroxymarcfortine derivatives of the natural products marcfortine A, B, C, and D useful in the treatment and prevention of helminth and arthropod infections of animals and plants. The synthetic derivatives are of Formula (I). STR1
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(2008/06/13)

Marcfortine/paraherquamide derivatives useful as antiparasitic agents
There are disclosed 18-thiomarcfortine derivatives of the natural products marcfortine A, B and C, C-18 thioparaherquamide and derivatives thereof, novel N-1 marcfortines A, B, and C and derivatives thereof, novel N-1 paraherquamide and derivatives thereof usefull in the treatment and prevention of helninth and arthropod infections of animals and plants. Any inquiry concerning this communication or earlier communications from the examiner should be directed to Examiner Robert T. Bond whose telephone number is (703)308-4711. The examiner can normally be reached on Monday through Friday from 8:00 AM to 4:30 PM.
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(2008/06/13)

Antiatherosclerotic and antithrombotic 1-benzopyran-4-ones and 2-amino-1,3-benzoxazine-4-ones
This invention relates to compounds of Formula I STR1 which are useful in association with a pharmaceutical carrier as antiatherosclerotic agents. In addition, various compounds of Formula I are useful inhibitors of cell proliferation.
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(2008/06/13)

Catalysis at Lonza: From metallic glasses to fine chemicals
At Lonza, a company which is backwards integrated to light virgin naphtha and liquefied petroleum gas, catalysis is used throughout the entire scale of value added products, starting from bulk chemicals and intermediates up to special fine chemicals. In addition, environmental catalysts are used in order to fulfil the high standards of Lonza's waste management concept. However, the need for the involvement of a dedicated catalysis group is mainly seen at the upper end of the product tree: with increasing diversification the catalysts have to match the complexity of the products and the demand for tailor-made catalysts is increasing. In this sense, also the potential of new catalytic materials is being examined at Lonza. In the following, two examples of a more fundamental approach (amorphous alloys and amorphous/nanocrystalline oxides as catalyst precursors) are given. In addition, a new synthesis of β-picoline is discussed as an example of a straightforward product-oriented approach.
Heveling, Josef
p. 114 - 118
(2007/10/03)

Novel and facile reduction of heterocyclic compounds with lanthanoid metal-hydrochloric acid system
Pyridines were rapidly reduced to piperidines with Sm or Yb-HCl system at room temperature in quantitative yields. Quinolines and isoquinolines were similarly reduced to the corresponding 1,2,3,4-tetrahydro-derivatives with Sm-HCl system in good yields.
Kamochi,Kudo
p. 1422 - 1424
(2007/10/02)

Addition-Elimination Mechanism of Aminolyses of 4-Nitrophenyl Benzoate and Its Sulfur Analogue
The aminolysis of O-(4-nitrophenyl) thiobenzoate proceeds via an addition-elimination mechanism in which the rate-determining step is dependent on both concentration and basicity of amines.
Um, Ik-Hwan,Kwon, Hye-Jin,Kwon, Dong-Sook
p. 1801 - 1817
(2007/10/03)

Antiatherosclerotic and antithrombotic 2-amino-6-phenyl-4H-pyran-4-ones
This invention relates to compounds of Formula I STR1 which are useful as antiatherosclerotic agents and inhibitors of cell proliferation for the treatment of proliferative diseases. In addition, various compounds of Formula I are useful inhibitors of platelet aggregation.
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(2008/06/13)

THE NOVEL REDUCTION OF PYRIDINE DERIVATIVES WITH SAMARIUM DIIODIDE
Pyridine was rapidly reduced into piperidine with samarium diiodide in the presence of water at room temperature in excellent yield.On the similar reactions of pyridine derivatives bearing chloro, amino and cyano functionalities with samarium diiodide-H2O-THF system, these functionalities were partly eliminated with this system to afford pyridine or piperidine.Furthermore, pyridinecarboxamides were reduced with this system to give the corresponding methylpyridines and 2-pyridinecarboxylic acid was reduced to give 2-methylpyridine as the major products.
Kamochi, Yasuko,Kudo, Tadahiro
p. 2383 - 2396
(2007/10/02)

Enamine quaternary compounds, methods of making and their use as muscle relaxants
Disclosed are novel enamine quaternary compounds of the formula STR1 wherein m=1, 2 or 3 and n=1, 2 or 3 with the proviso that m+n=3, 4 or 5; R1 and R2 are independently lower alkyl or hydrogen, and R3 and R4 are independently selected from the group consisting of lower alkyl, lower cycloalkyl lower alkyl, lower alkenyl, phenyl lower alkyl, thienyl lower alkyl, furyl lower alkyl, lower alkoxy lower alkyl, halogenated lower alkyl, lower alkyloyloxo or lower alkyloyloxy lower alkyl or wherein NR3 R4 together comprise a heterocycle ring; and wherein X- represents a pharmaceutically acceptable anion. Pharmaceutical compositions containing the same when administered to warm-blooded animals exhibit a muscle relaxant effect characterized by excellent onset and recovery times. Also disclosed are methods of making the enamine quaternary compounds.
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(2008/06/13)

Treatment of atherosclerosis with khellin-related furochromones
The present specification relates to the antiatherosclerotic use of khellin and related furochromones, and further provides novel antiatherogenic furochromones.
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(2008/06/13)

Antiatherosclerotic furochromones
The present specification relates to the antiatherosclerotic use of khellin and related furochromones, and further provides novel antiatherogenic furochromones.
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(2008/06/13)

1,3-Diaminomethyl-hydantoin additives for lubricating oils
Lubricating oil compositions, comprising as additive, from 0.001 to 10% by weight, based on the weight of the total composition, of a 1- or 3-aminomethyl-hydantoin or a 1,3-diaminomethyl-hydantoin.
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(2008/06/13)

Anthelmintic 5(6)-benzene ring substituted benzimidazole-2-carbamates
Benzene ring substituted benzimidazole-2-carbamate derivatives represented by the formula: STR1 where R is a lower alkyl group having 1 to 4 carbon atoms; STR2 is a 5, 6, 7 or 8 membered heterocyclic ring containing 1 to 2 hetero atoms; the STR3 substitution being at the 5(6)-position; and the pharmaceutically acceptable salts thereof. The compounds are useful as pesticides, particularly as anthelmintic and antifungal agents.
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(2008/06/13)

3,6-Bis-(heterocyclic aminoacyl-amino)-acridines and salts thereof
Compounds of the formula STR1 wherein R1 is hydrogen or methyl, R2 and R3, together with each other and the nitrogen atom to which they are attached, form a saturated or unsaturated heterocyclic ring system which may optionally contain one or more additional heteroatoms, and A is lower alkylene or aryl-lower alkylene, and nontoxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as their salts are useful as inducers of the formation of interferon.
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(2008/06/13)